Hydrochloric Acid → HCID 15289699, compound

HRID 37495Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=2)[N:3]=1.Cl>C(O)C>[NH2:18][C:5]1[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=2)=[N:3][C:2]([Cl:1])=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

Conditions

Temperature: 60 °C

Procedure

In 8 ml of ethanol were suspended 0.37 g of 2-chloro-3,4-diethoxycarbonyl-5-nitro-6-(3-nitrophenyl)pyridine and 0.45 g of reduced iron, and the suspension was heated to 60° C. After 1.9 ml of conc. hydrochloric acid was added thereto, the mixture was heated for 30 minutes under reflux. After the reaction mixture was concentrated, the residue was extracted with ethyl acetate, followed by washing with an aqueous solution of sodium hydrogencarbonate and an aqueous solution of sodium chloride and drying over magnesium sulfate. After the extract was concentrated under reduced pressure, the residue was subjected to silica gel column chromatography (eluent: chloroform/methanol 40:1) to give 0.29 g of the title compound as a yellowish orange viscous oily substance.

Workup

temperaturethe mixture was heated for 30 minutes
temperatureunder reflux
concentrationAfter the reaction mixture was concentrated
extractionthe residue was extracted with ethyl acetate
washby washing with an aqueous solution of sodium hydrogencarbonate
dry with materialan aqueous solution of sodium chloride and drying over magnesium sulfate
concentrationAfter the extract was concentrated under reduced pressure

Sources & evidence

ORD record: ord-1f282d272c8142f4b01c5fd3688f491d
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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